50 Best Bermuda Vacation rentals on Holiday Lettings - Estates

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Southampton Parish
12 properties
Smith's Parish
10 properties
Pembroke Parish
9 properties
St. George's Parish
9 properties
Warwick Parish
7 properties

Bermuda

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54 Vacation rentals

(4) Excellent 

12

South Shore Vacation apartment rental

Southampton Parish / South Shore

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
A contemporary ocean-front apartment with access to a horizon pool located at the end of a quiet lane on the south shore between West Whale Bay and Church Bay. Ideal for those looking to relax, with panoramic ocean views from every room and a private lawn where you can …see more

from $295 / night

$2065 / week

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from $295 / night

17

Bermuda Vacation studio rental

Bermuda / Southampton Parish

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Private and cozy studio located on a hill which gives you a breathtaking view of Jews Bay and Dockyard (home of the Americas Cup). The studio is part of a large house with a separate entrance. It is fully furnished - comfortable queen size bed, love seat, dining for 2, …see more

from $150 / night

$1050 / week

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from $150 / night

25

Bermuda Vacation home rental

Bermuda / Paget Parish

7 14 1 night min

  • 7 bedrooms
  • Sleeps 14
  • 1 night min
  • Child friendly
Sprawling graciously , in a park like setting, filled with grand old majestic trees, sits this five bedroom five and a half bathroom entertainer's paradise. Behind the enchanting traditional Bermuda façade lies a modern interpretation of sophisticated and care-free urba …see more

from $1189 / night

$8320 - $11648 / week

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from $1189 / night

(1) Excellent 

9

Vacation home with shared pool in Smith's Parish

Bermuda / Smith's Parish

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
The pool house is a studio and has a queen bed and its own bathroom + shower. It is next to our house in a spacious yard in a quiet residential neighborhood. Bus stop is a 3 minute walk, beautiful John Smith's Bay beach is a 5 minute walk and a grocery store is a 10 min …see more

from $165 / night

$1085 / week

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from $165 / night

14

Vacation cottage with shared pool in Bermuda

St. George's Parish / St. George

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
1 WEEK ONLY!!! TIME SHARE !!!FREE STANDING COTTAGE HOME IN PRIVATE SETTING WITH POOL STEPS AWAY. MASTER SUITE, IS ON 2ND FLR FEATURES SOAK TUB, SHOWER & DOUBLE VANITY.HAS BALCONY WITH VIEWS. 2ND PRIVATE BEDRM ON 1ST FLOOR HAS 2 TWIN BEDS & 2ND FULL BATH. LIVING RM HAS H …see more

from $458 / night

$3200 / week

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from $458 / night

(15) Very Good 

10

Vacation cottage in Bermuda

St. George's Parish / St. George

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Child friendly
Experience your Bermuda vacation in the World Heritage Town of St Georges! This traditional Bermuda cottage has been thoroughly updated and modernized whilst retaining charm and character. Amenities include an en-suite master bedroom with King size bed, a modern fully …see more

from $150 / night

$950 / week

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from $150 / night

12

Vacation apartment in Bermuda

St. George's Parish / St. George

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Newly renovated accommodation in a large garden setting located in the heart of the old town of St George's includes Continental Breakfast.Close to Ferry and bus routes,local corner store,restaurants and shops. On the property their is use of BBQ with outdoor dining fa …see more

from $125 / night

$875 / week

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from $125 / night

(1) Excellent 

17

Bermuda Vacation cottage rental

Bermuda / Sandys Parish

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
The Ledgelets Cottage Colony is located just past the worlds smallest drawbridge, Somerset Bridge. No longer a working drawbridge today, it does connect you to our little piece of "The Rock". The property is situated in just below Fort Scaur on 4.5 acres, featuring love …see more

from $250 / night

$1750 / week

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from $250 / night

33

Vacation home in Bermuda

St. George's Parish / St. George

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Beautiful 1,507 sq. ft. vacation rental. Two BR luxury home; kitchen; large DR; relaxing LR with a dinette set, fireplace and a sleeper sofa for two; laundry room; master bedroom with spa bathroom and fireplace; AC/Heating units; four flat screen TVs, two large porches …see more

from $350 / night

$2450 / week

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from $350 / night

(4) Very Good 

12

Apartment rental in Hamilton Parish

Bermuda / Hamilton Parish

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
'Neston' is on 2 acres of property, located in a very quiet and secluded neighborhood. Enjoy the Beautiful Views of Harrington Sound one of the most Beautiful inlets in Bermuda. Harrington Sound is a wonderful inland lake in Bermuda surrounded mainly by Hamilto …see more

from $195 / night

$1365 / week

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from $195 / night

18

Smith's Parish Vacation b&b rental

Bermuda / Smith's Parish

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 1 mi
  • Air conditioning
The Queen bedroom has a separate bathroom, large double closet, individual air conditioning, ceiling fan with tray ceiling. Cloud High is a charming house with it's sunny and bright ambiance. The living room is large with comfortable upholstered furniture with cable TV. …see more

from $150 / night

$1050 / week

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from $150 / night

(1) Excellent 

21

Vacation studio with swimming pool, tennis court in Paget Parish

Bermuda / Paget Parish

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
•Consistently rated 5★★★★★ •Your OWN Private Pool & Tennis Court •Walk to Hamilton •5 min. ride to Elbow Beach •High speed Internet •New Pillow-top, king-sized bed •Fully equipped + stocked kitchen •Near bus stops to both ends of the island •42" TV •Extremely safe neigh …see more

from $179 / night

$1253 / week

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from $179 / night

(6) Excellent 

15

Bermuda Vacation home rental

Bermuda / Warwick Parish

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Sunscape Bermuda is a handsome house standing on top of Lusher Hill exhibiting breathtaking views of the entire island. It is only 5 minutes by moped to the beautiful sands of Warwick Long Bay and just a stroll from there to the Horseshoe Bay. The parish of Warwick is r …see more

from $200 / night

$1400 / week

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from $200 / night

22

Vacation home in Bermuda

Bermuda / Warwick Parish

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Nearest beach 3 mi
  • Child friendly
  • Car not necessary
The house is tucked privately off of the main South Shore Road in Bermuda. It is in a beautifully, safe location that is walking distance to restaurants, a one-stop gas station, the best beaches and public transportation. This unit is a 2 bedroom apartment that rents fo …see more

from $249 / night

$1743 / week

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from $249 / night

(5) Excellent 

4

Vacation studio with shared pool in Bermuda

Pembroke Parish / Hamilton

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
Hibiscus Hideaway is a self-catered, studio accommodation for tourists and business travelers, located in a serene and very convenient location. A pleasant 5-minute walk into the heart of Hamilton, making all of the amenities easily accessible (shops, restaurants, groce …see more

from $150 / night

$1050 - $1400 / week

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from $150 / night

20

Bermuda Vacation home rental

Bermuda / Southampton Parish

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min
  • Child friendly
The Four C's is situated in a prime location for vacationers. Situated just off of the South Shore Road between Horseshoe Bay Beach and Church Bay Beach only a very short walk to Cross Bay Beach your private beach, where you can enjoy endless hours in the Sun and Surf. …see more

from $680 / night

$4760 / week

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from $680 / night

(1) Very Good 

16

Vacation apartment in Bermuda

Bermuda / Hamilton Parish

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Attractive lower apartment on a property with panoramic seascape views of North Shore Bermuda. Extra features include excursions to Bermuda Railway trail, fishing off of Bay Island, visits to nearby Crystal Caves (we are descendants of the discoverers) and Grotto Bay Ca …see more

from $70 / night

$490 / week

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from $70 / night

(1) Very Good 

4

Vacation apartment in St. George

St. George's Parish / St. George

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
A Historic, elegant family home in a quiet neighbourhood within a 5 minute walk to the town centre and bus stops. St. George's harbour (alongside the town centre) is the site for the new marina coming in 2016 and currently has facilities for visiting yachts. Closest bea …see more

from $165 / night

$1155 / week

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from $165 / night

48

Bermuda Vacation home rental

Bermuda / Warwick Parish

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
This is a small neighborhood in a great location. Children love that there is a lot of space to run and play. The adults love that they have their own private outdoor area. Ocean Sounds is close to the beaches. It is good for couples, business travelers, families (with …see more

from $500 / night

$7140 - $7840 / week

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from $500 / night

(1) Excellent 

9

Vacation apartment with shared pool in Bermuda

Bermuda / Smith's Parish

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
The apartment is close to the beautiful John Smiths Bay beach - an 8 minute walk away. The pool is on the property and around the back from the apartment. The apartment has a queen bed and its own bathroom + shower. It is next to our house in a spacious yard in a quiet …see more

from $120 / night

$770 - $1015 / week

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from $120 / night

(7) Excellent 

17

Vacation home in St. George

St. George's Parish / St. George

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.5 mi
  • Ask about children
  • Air conditioning
1768 historic Bermuda cottage, restored with modern conveniences, situated in the Town of St George and just walking distance to beautiful beaches and historic forts as well as restaurants and shops. Cottage is set in a landscaped garden with tropical fruit trees and ea …see more

from $175 / night

$1225 / week

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from $175 / night

(1) Excellent 

7

Vacation apartment in Bermuda

Pembroke Parish / Hamilton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
Relax on the porch and enjoy the view of one of the most beautiful harbours in the world. These apartments are situated in a quiet secluded neighborhood that can be enjoyed by foot to explore its beautiful homes, gardens, and bays. Minutes away by moped or taxi are the …see more

from $245 / night

$1600 / week

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from $245 / night

6

Apartment rental in Hamilton

Pembroke Parish / Hamilton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
Relax on the porch and enjoy the view of one of the most beautiful harbours in the world. These apartments are situated in a quiet secluded neighborhood that can be enjoyed by foot to explore its beautiful homes, gardens, and bays. Minutes away by moped or taxi are the …see more

from $235 / night

$1500 / week

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from $235 / night

26

Vacation studio in Bermuda

Sandys Parish / Somerset Village

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This studio sits in the heart of Somerset Village in Sandys, Bermuda. Easily an ideal place for couples visiting Bermuda without transportation. Its the perfect spot with a restaurant across the street, local shops, beaches, bus stops and other entertainment within clos …see more

from $200 / night

$1400 / week

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from $200 / night

(5) Excellent 

12

Vacation apartment in Bermuda

Bermuda / Pembroke Parish

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
It really isn't too late to come and experience the hidden gem of Bermuda and live like the locals do in a safe, family-like neighbourhood. Located on the north side of Bermuda amongst two spectacular parks, with caves that you can explore right at your finger tips. Cen …see more

from $125 / night

$875 / week

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from $125 / night

(1) Excellent 

17

Bermuda Vacation studio rental

Sandys Parish / Somerset Village

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Air conditioning
This studio sits in the heart of Somerset Village in Sandys, Bermuda. Easily an ideal place for couples visiting Bermuda without transportation. Its the perfect spot with a restaurant across the street, local shops, beaches, bus stops and entertainment within close prox …see more

from $200 / night

$1400 / week

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from $200 / night

13

Vacation apartment with golf nearby in Bermuda

Bermuda / Southampton Parish

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
The Rising Sun is located on the waters of Jews Bay with stunning water views from every room. There is a private dock which offers easy access to the water. We are directly on the bus route to Dockyard and Hamilton. There are spacious upper and lower verandas overlooki …see more

from $575 / night

$3626 - $4725 / week

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from $575 / night

(8) Excellent 

8

Hamilton Vacation apartment rental

Pembroke Parish / Hamilton

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning
Relax on the porch and enjoy the view of one of the most beautiful harbours in the world. These apartments are situated in a quiet secluded neighborhood that can be enjoyed by foot to explore its beautiful homes, gardens, and bays. Minutes away by moped or taxi are the …see more

from $120 / night

$800 - $1300 / week

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from $120 / night

(4) Excellent 

15

Vacation home in Bermuda

St. George's Parish / Tucker's Town

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Air conditioning
  • Private garden
This house sits on the Mid-Ocean Golf Club between the 16th and 17thh fairways in Bermuda overlooking Castle Harbour and the outlying islands. There are 2 bedrooms with bathrooms ensuite, one with king sized bed and the other with queen sized bed. There is also a powde …see more

from $500 / night

$3500 - $4200 / week

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from $500 / night

(3) Very Good 

18

Vacation b&b in St. George

St. George's Parish / St. George

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
Aunt Nea's Inn is a historic Bermudian guest house located in the UNESCO World Heritage site of St. George's. From original woodwork and building craftsmanship from the 1700s to stunning harbour and garden views, you will love staying in this very special property in th …see more

from $195 / night

$1365 / week

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from $195 / night

14

Vacation cottage in Bermuda

Bermuda / Southampton Parish

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
Adorable stand alone cottage located in Southampton with stunning views of the Great Sound. The cottage itself consists of two bedrooms, one bathroom, eat-in kitchen, a living room with fireplace, a covered porch and a lower level laundry room. The cottage has two acces …see more

from $198 / night

$1380 / week

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from $198 / night

(12) Very Good 

5

Vacation apartment rental

Pembroke Parish / Hamilton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Car not necessary
  • Air conditioning
A stone's throw from the city of Hamilton, this apartment offers views of the city skyline. We are located in a residential neighbourhood which is conveniently located close to schools, churches, grocery stores and the city center. Just about everything you need is with …see more

from $140 / night

$815 / week

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from $140 / night

(1) Excellent 

6

Vacation apartment in Bermuda

Bermuda / Warwick Parish

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Child friendly
  • Air conditioning
  • Private garden
This is a spacious one bedroom apartment with all the luxuries of home including air conditioners, smart tv, free wifi, microwave, dishwasher and a clack back couch bed. The unit is tiled throughout. The bedroom has it's own private patio outside with ocean views, a …see more

from $129 / night

$903 / week

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from $129 / night

(3) Excellent 

11

Vacation apartment in Warwick Parish

Bermuda / Warwick Parish

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
This cute studio is spacious and comes with all the amenities needed to create a home away from home. The main room is 29ft x 16 and it comes with an open space sleeping and living quarters. The separate kitchen consists of a washer/dryer combo, stainless steel gas …see more

from $159 / night

$1113 / week

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from $159 / night

(2) Excellent 

16

Apartment rental in Bermuda

Bermuda / Warwick Parish

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
This beautiful property is located on the South Shore close to all the popular beaches and directly across from Warwick Long Bay which was listed by CNN as one of the top beaches in the world. This unit is just steps away from the bus stop and the playground ... for tho …see more

from $250 / night

$1680 / week

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from $250 / night

26

Vacation home rental

Bermuda / Smith's Parish

5 10 14 nights min

  • 5 bedrooms
  • Sleeps 10
  • 14 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
You’ll love this property because of the pool and great outdoors entertaining space with a gas grill, as well as the very comfortable living room, kitchen and den area. This property is great for groups i.e. up to 4 couples or families. It is also very close to the beau …see more

from $1200 / night

$8400 / week

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from $1200 / night

(1) Very Good 

8

Vacation apartment in Bermuda

Pembroke Parish / Hamilton

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Air conditioning
Relax on the porch and enjoy the view of one of the most beautiful harbours in the world. These apartments are situated in a quiet secluded neighborhood that can be enjoyed by foot to explore its beautiful homes, gardens, and bays. Minutes away by moped or taxi are the …see more

from $210 / night

$1400 / week

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from $210 / night

23

Apartment rental in Bermuda

Bermuda / Smith's Parish

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Large one bedroom apartment located off of Knapton Hill in Smith's in a very private neighborhood. Very spacious and in a private garden setting. Lovely to sit off on the patio after a long day at the beach or out on the water. Galley Kitchen opening up onto large li …see more

from $185 / night

$1165 - $2330 / week

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from $185 / night

(4) Excellent 

24

Vacation apartment with shared pool in Bermuda

Bermuda / Smith's Parish

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.75 mi
  • Swimming pool
Watch Hill Manor is conveniently located only 12 minutes from the Bermuda's International Airport, in Smith's Parish. The property looks East, overlooking the John Smith's Bay area and the beautiful South Shore, down as far as Castle Roads and Bird Rock. The property i …see more

from $220 / night

$1540 - $1680 / week

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from $220 / night

25

Vacation home in Bermuda

Bermuda / Southampton Parish

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
This lovely waterfront home has stunning views of the Great Sound and consists of 4 bedrooms with 4 bathrooms. The master bed with a king bed, two guest rooms with two twins and the other guest room with a double bed. There is a large formal living room with wood burnin …see more

from $750 / night

$5244 / week

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from $750 / night

1